Having to Choose
by caroline-reid
Summary: Dean has to choose between his sister, his little princess, or Lisa, his ex-girlfriend, whom which he still loves. Sam really should've insisted he got the food. Takes place in the middle of Season 6.


Title: Having to Choose  
Disclaimer: I don't own any Supernatural characters or stores mentioned. Alas, I only own Riley and the Demon woman.  
Pairings: LisaxDean happened before this occurrence.  
Summary: Dean has to choose between his sister, his little princess, or Lisa, his ex-girlfriend, whom which he still loves. Sam really should've insisted he got the food. Takes place in the middle of Season 6. Slightlydouchebag!Dean,

Riley Winchester sat in the cold cell, alone and tied with her hands behind her back to a wooden pillar. "_HELLO!_" The basement she was in was empty par of her and other wooden pillars. She tried getting her hands out from the rope tie, only succeeding in getting rope burn on her wrists.

"_Hello?_" She whispered. Time felt like it passed slowly. It had most likely been thirty minutes but felt like an hour. A door higher up and to the left opened up. A woman was being carried down by a Demon, one they had been trying to capture for close to four days. Sam had found out she was kidnapping women, torturing them and then killing them in their own homes.

Riley closed her eyes, willing herself not to cry and to believe in her brothers. They were smart, they would figure out she was gone. _It's not like I have that much of a choice._

"Dean, when's Riles getting back with the food?" Sam looked up from his laptop, his stomach rumbling softly. He'd been looking up the vics, trying to see if they could find where a common place was for all of them.

"I dunno. She left like an hour and a half ago. I'll go see if I can spot her." Dean shrugged, not all too concerned. She had mostly likely been side-tracked by something, as usual, and forget about what her purpose was in the first place. She once went on a food trip and came back three hours later rambling about Picasso and Van Gogh.

"Alright, get food on the way back, too. I'm starving." Dean nodded absently, grabbing his leather jacket and keys before closing the door behind him. _I'll start at the McDonald's we passed on the way here_.

Riley woke up to the sound of angry screams. "FUCK YOU!" She heard the woman yell.

"Geez, lady, you got some lungs." Riley was about to reach up and rub her eyes to chase away the sleep before realizing she was still tied up.

"Who are you? Where's my son?" Riley rolled her eyes, silently praying the woman get herself killed. "I said, _who are you_?" Riley huffed.

"Riley, fourteen. How in the hell am I supposed to know where your son is?" Riley tried to get her wrists free, again not working. "Who're you?" Riley blew air from her mouth, trying to get her blonde hair out of her face. She looked to the woman with her green eyes, staring.

"Lisa. My son, Ben, was with me when I was taken." Riley sucked in a breath, willing time to pass. Since she fell asleep, she had no idea how long it had been since she was taken. _Where are you, Sam? I need you._

"Sam, I can't find her!" Dean yelled, slamming the front door of their motel room closed. Sam looked up. "I looked _everywhere. _McDonalds, Wal-Mart, White Castle, Target. I fricken' looked in the art museum! Wasn't studying some lame art with a hot dude." Dean put down the bag of fast food he'd picked up for him and his brother.

"Well, one thing I found, is that the Demon picks up the vics from this bar, Baxter's Bar, then takes them back to their place. We could try there. Maybe Riley was in sight from the entrance and the Demon picked up on her?"

"Alright. Hurry up and eat. We're gonna go down to the Bar, see if anybody saw her." Sam wolfed down the cheeseburger, stashing the to-go coffee cup to drink in the Impala. They were out the door in minutes.

"Hello, darlings," Demon-woman stood in the doorway, at the top of the steps. "I just want to let you too fine specimens that may be waiting for a little way until the little-Winchester girl's older brother's catch up. I suggest you play ni-" The Demon stepped down the wooden steps slowly, watching Lisa and Riley carefully.

"What have you done with Ben!" Lisa screamed, her brown hair flinging around. Riley sat back, her thick wavy blonde hair pushed away from her face, "Wait. Winchester? _Dean _Winchester?" Lisa looked to Riley, narrowing her eyes.

"Yep. Dean's my oldest brother." Riley shrugged, stretching out her arms to do so. Demon-woman watched, bored.

"Ben is safe. He'll be waiting for you to get back." With that, the Demon woman waved her hand. "That's all I'll say for now. Ta ta, girls. Nice chatting with you." Demon woman retreated back up the stairs.

"You know they'll kill you, right! Sam and Dean kill Monsters! They'll easily exorcise you right back to Hell." Riley shouted up to the Demon, right before she closed the door, "You'll be minced meat once they find you."

"Well, you'll be minced meat _when _they find you." The Demon winked, her eyes flashing wholly black before laughing and closing the door with a clang.

"Excuse me, Agent Foreman, Agent Johnson, FBI. Have you seen this little girl walking around outside at all?" Dean held up his FBI badge next to Sam's before taking out their latest picture of Riley, her a month ago, sleeping on a bed of a motel, curled up and cute.

"Uh, yeah, actually. Like, four hours ago, I guess. Why? Is she in any kind of trouble? Looked like a real sweet kid." Marie the barista nodded, looking at the clock before back to the two men.

"No, no, not at all. We were just in the area and her parents contacted us. Decided to take a quick look. One last question; was she holding anything or was she just walking?" Sam waved off her concern, assuring her.

"She had a bag of food with her. From what I could see it looked like pie, ice cream, and spaghetti stuff." Marie shrugged. "Wish I could help more but I didn't see anything else, I was helping a customer."

"Thank you for you for everything, Miss. Contact us if you remember anything." Dean took out their FBI contact card, handing it to the barista. "Have a good day."

"Well, that was a whole bunch of nothin'," Dean grunted, walking across the street to the Impala. He opened the driver seat, "Where to next?"

"Wait, Dean, do you smell that?" Sam sniffed the air again. Dean sniffed once before widening his eyes and closing his door.

"I know that smell, anywhere. That's the smell of pie." Dean took a big breathe through his nose, walking back into the alley beside the Baxter's Bar. There, they found a grocery bag of pie, melted mint chocolate chip ice cream, with noodles and spaghetti sauce.

"So, what, the Demon dragged Riley back here and then just took her? Did she know who she was?" Sam asked, looking around the area for any more clues.

"She is a Winchester, Sam. Practically every Supernatural thing in the U.S. knows who we are." Dean rolled his eyes. "We also taught her how to tell us where they took her. C'mon, Sammy, what do you do if you're conscious and being taken somewhere by a Demon?" Dean turned to Sam, remembering every step and counter-measure, wanting to know if Sam remembered.

"Well, you kick off a shoe once you're a little bit away, so there's a trail." Sam nodded, looking around. He walked out of the alley way, turning his head to look both ways. Down to two blocks to the left, peeked a bright red shoe. Dean and Sam made their way to the shoe, picking it up. Underneath the shoe in scribbled letters was 'RILES'. "The shoe's by the curb so she probably kicked it off when she got into a car."

"And what do you do when you get into a trunk?" Dean looked both ways of the street before Sam answered,

"You kick out a tail gate, piece by piece." Sam looked both ways as well, the pieces starting down four blocks to the right. "Alright, if we follow the pieces, we should be getting close." Sam and Dean got into the Impala, driving slowly down the roads, looking for pieces in the middle of the road.

"You're brothers should be here any minute. I can smell them getting close." Riley puffed her breathe in annoyance when the Demon woman came back downstairs, "Oh, don't play that, Honey. We both know you didn't have a plan of getting out."

"It's not like you put up a giant sign saying, '_This is where I've hid them. Come and get'em, boys._'How do you think they got here?" Riley rolled her eyes, tired. She may slept for a bit but at the same time, she no doubt had bruises on her wrists and her abdomen from struggling.

"I suppose you're right. I've got a quick question for you two, did either one of you consider why I have Dean's little sister and Dean's ex-lover, whom which he was with for a year. I mean, he even gave his little adopted-sister to Bobby Singer to watch over while Sam was gone."

That comment made Lisa's eyes widen, as well as Riley mutter, "_Fuck._" under her breathe. "You're going to make him choose." It wasn't a question. A simple statement. The little sister your younger brother and Dad wanted to adopt when you were 20, her being 2, you not wanting another mouth to feed or the ex-lover who you spent a year with her and her son while you dropped your 13 year old sister off at your pseudo-father's house."

Riley argued with herself. Dean may not have always specifically loved her, been more guarded around her, but she was family. _So is Lisa. Lisa and Ben are Dean's family, too. _All she could do was hope they managed a way to pick both. Demon woman moved both Lisa and Riley to the middle of the room, facing the door while they were both silent and contemplative.

"They're most likely checking every other room." Lisa and Riley sat in their places, backs hunched, for twenty minutes before the sound of stomping footsteps sounded throughout the house, "You know, they're really loud. They should quiet down." The Demon _tut-tut_'d them before laughing. She tried pet Riley's hair but Riley flung her head away from the Demon, not wanting to be touched by her. "I am going to have _so _much fun with this."

The door was kicked open, _Probably Dean_, letting Sam and Dean run down the stairs. Before they got very far, Sam was flung to the cement wall to the right of the staircase from their view point, pinned and immobile. Dean was given the same treatment only to the floor, slowly brought up to being on his knees. "Hey, Dean. Hey, Sam. How're you guys? I'm pretty great, I've got two lovely women as company. Anyways, you probably want to know what this is about."

"Give them back, you son of a bitch!" Dean gruffly yelled. Both brothers were trying a valiant rescue, get both girls out, gank the Demon, everyone goes home safe. Sam was wrestling against the strength of the Demon with Dean just staring at the women.

"Ah, ah, aaah. I haven't told you why I took them in the first place." Demon-woman put her hands on her hips, shaking her head. She turned, lifting her right hand and made a poking motion towards Lisa, resulting in her coughing up a little blood. "Anyways, as I was saying… Here's how it's gonna go. Dean, you have to choose. Lisa, or Riley? Sam, you get to watch. Riley, Lisa, you two get to look pretty for the contestant and hope he picks you. So, Dean, who's it gonna be?"

Dean looked back and forth from everyone quickly, the Demon letting him move he head freely. "Dean! What're you thinking! Riley!" Sam yelled, looking anguished. Lisa closed her eyes tightly, expecting that she'd be killed.

"C'mon, Dean, who's it going to be? The thorn in your side for a good 12 years or someone you actually love? Tick tock, tick tock, tick tock." The Demon woman made a motion of looking at her watch, counting the seconds.

"Riley, I am so sorry." Dean looked from her to Lisa to the Demon and back to her. "Ben needs her. Please forgive me. I will find a way to fix this." Riley cried silently, nodding. "I pick Lisa." He looked the Demon in the eye, determined. The Demon woman untied Lisa's ropes, threw her to Dean, unlocking him from his place while he tended to Lisa.

"NO! DEAN, WHAT ARE YOU DOING!" Sam kept trying to push against the hold of the Demon while on the wall, trying now harder than ever. His older brother was picking an old girlfriend over his little baby sister. "DEAN! HOW COULD YOU? IT'S _RILEY_."

"No, Sam, it-it's okay. I understand. I-I love you both and I for-" Riley's sentence was cut short, a cut appearing across her neck. The Demon woman laughed before going up the stairs,

"I'll be in the living room, waiting for you boys to be done." Blood oozed out of Riley, her body dropping to the floor from her Indian style sitting position. Sam fell from the wall once the basement door was fully closed, running to his fourteen year old sister.

"Riley!" Dean stayed back, tending to Lisa's stomach wound while Sam sat beside his baby sister, "Shh, shh, it's okay, Riley. You're gonna be okay." Riley's eyes distanced, "It's just a flesh wound, you're fine. Dad- Dad's gonna get here and we're gonna fix you, good as new. I-I promise. I love you, Riles. My little princess. Do you remember that time you-you skinned your knee? You were running too fast," Riley's eyes closed but Sam didn't notice, stroking her blonde hair, "You- you were crying and I saw. I gave you a band-aid and said that you fell so that a prince could pick you back up. It-it's just like then. Your prince will be here soon." Sam sat there, holding his little sister, crying.

"Sam…" Dean came up behind Sam, reaching for his shoulder. Sam wrenched out of the way, not wanting to be touched my the Monster that his brother was. Dean sighed, turning back to Lisa, "I'm gonna go take care of that Demon. I'll be right back." He popped the sword out from a sheath in his belt, heading up the stairs.

"Sam, I'm sorr-" Lisa started, looking at Dean's siblings, huddled.

"Don't." Sam's cold voice broke through. It sounded eerily similar to when he was soulless, though Lisa didn't know that. "_You _killed her." Sam looked over his shoulder, tear tracks down his cheeks, glaring. They heard a scream and a laugh gargled together before it went silent. Dean came back down the wooden stairs,

"Well, she's dead." Dean walked over to Sam and Riley, touching Sam's shoulder, "Sam, didn't you hear me? She's dead." Sam gently laid Riley down, brushing her hair away from her face before getting up, dusting off his thighs carefully, and punching Dean in the face.

Dean fell down, trying to block his face while Sam whaled on him. Lisa sat in shock before getting up and trying to break up the one-way fight. "YEAH! SHE IS DEAD, DEAN. YOU KILLED HER. RILEY EMMELINE WINCHESTER IS DEAD. BECAUSE OF YOU. I hope you have to tell Bobby and Cas what you've done because so help me, God, if you don't. If I have to sit in front of Bobby, and tell him, that his daughter, his family is dead because of you or if you even call them over the phone then you better hope you can run, Dean." Sam stopped beating on him after he gave Dean's face the promise of a couple of upcoming bruises, the same to his chest.

"I'm carrying her to the car-" Dean winced at the thought of blood on his Impala seats. "And if you try and stop me, I will punch your face off." Sam put his right arm under knee, putting his left arm behind her back and lifting her carefully. Up the stairs, and into the Impala.

After laying her carefully down in the backseat, Sam took the driver's seat, Dean in passenger with Lisa sitting in the back seat next to Riley's curled up feet. Sam took off, stopping at the motel, grabbing stuff, throwing it in the trunk, and then driving so fast, the building was left behind them within a matter of minutes.

If only he could all leave the memories behind…


End file.
